Author: Jessica.F

Reference of 710-18-9, In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 710-18-9 as follows.

General procedure: Lewis acid (1.0-1.5eq) (powdered AlCl3, powdered FeCl3, 1 or 2 M solution of TiCl4 in CH2Cl2) was added portionwise to a stirred 1 M solution of the aromatic compound in dry CH2Cl2, and then 2a-f (1.2-1.5 eq) was added dropwise at 0C over a period of 2-10 min. The mixture was stirred for several hours at room temperature. Following complete conversion of starting material, as confirmed by GC analysis, the mixture was quenched with H2O and extracted with CH2Cl2 or EtOAc. The combined organic layers were successively washed with satd. aq. NaHCO3 and brine, dried over Na2SO4, and concentrated in vacuo. The residue was purified by distillation or column chromatography on silica-gel, if necessary.

According to the analysis of related databases, 710-18-9, the application of this compound in the production field has become more and more popular.

Reference:
Article; Warashina, Takuya; Matsuura, Daisuke; Kimura, Yoshikazu; Chemical and Pharmaceutical Bulletin; vol. 67; 6; (2019); p. 587 – 593;,
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Application of 450-91-9, These common heterocyclic compound, 450-91-9, name is 4-Fluoro-2-methoxyaniline, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

To a mixture of 4-fluoro-2-methoxyaniline (25.0 g, 177 mmol), K2C03 (36.7 g, 266 mmol) and Nal (10.6 g, 0.07 mmol) in /- PrOH (250 ml.) was added bis(2-chloroethyl)amine hydrochloride (47 g, 177 mmol). The reaction mixture was refluxed overnight. The solvent was removed and the residue was purified by column chromatography (petroleum ether/EtOAc = 10:1 ) to provide 1 -(4-fluoro-2-methoxyphenyl)piperazine. MS: m/z 212.36 [M+H] +.

The synthetic route of 450-91-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; KEZAR LIFE SCIENCES; JOHNSON, Henry; (166 pag.)WO2019/178510; (2019); A1;,
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Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 41789-95-1, name is 1-(3-Methoxyphenyl)-N-methylmethanamine, A new synthetic method of this compound is introduced below., SDS of cas: 41789-95-1

General procedure: A mixture of Pd(OAc)2 (6.7 mg, 0.030 mmol, 10 mmol%), Cu(OAc)2 (54.45 mg, 0.30 mmol, 1 equiv.), 1a (32.1 mg, 0.30 mmol, 1equiv.), CsF (136.7 mg, 0.90 mmol, 3 equiv.) was dissolved in a solvent of acetonitrile (3 mL) followed by addition of 2a (179 mg,0.60 mmol, 2 equiv.). The reaction mixture was stirred at 120 C for 24 h and progress of the reaction was monitored continuously byTLC with ethyl acetate: hexane eluent system. Upon completion of reaction the mixture was cooled to room temperature, poured into brine, and extracted with EtOAc. The combined extracts were dried over MgSO4 and filtered through pad of Celite eluting with ethylacetate. The filtrate was concentrated under reduced pressure and was purified by column chromatography (EtOAc/hexane) on silicagel to afford the 5,6-dihydrophenanthridine 3a. Compound 1i was synthesized in accordance with reported literature [25]. Characterization data of compounds 3a, 3c, and 3e were found exactly similar as reported in the literature (References of above compounds are mentioned in Supplementary data).

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Article; Asamdi, Manjoorahmed; Chauhan, Prakashsingh M.; Patel, Janki J.; Chikhalia, Kishor H.; Tetrahedron; vol. 75; 25; (2019); p. 3485 – 3494;,
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These common heterocyclic compound, 75148-49-1, name is 3-Bromobenzaldehyde Diethyl Acetal, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. Formula: C11H15BrO2

Step 1: Preparation of 3-(3-aminooxetan-3-yl)benzaldehyde Hydrochloride 3-Bromobenzaldehyde diethyl acetal (11.65 g, 45 mmol) in dry THF (100 mL) at -78 C. was added n-butyl lithium (2.5 M in hexanes, 19 mL, 47 mmol) dropwise. The sample was stirred at -78 C. for ten minutes then added 2-methyl-N-(oxetan-3-ylidene)propane-2-sulfonamide (7.5 g, 43 mmol) dropwise. The sample was stirred at -78 C. for one hour. The mixture was diluted with 200 mL saturated ammonium chloride solution and 200 mL ethyl acetate. The layers were shaken and separated and the organic phase was dried over magnesium sulfate and concentrated under reduced pressure. The crude mixture was dissolved in ethyl acetate (250 mL). The reaction mixture was cooled to 0 C. was added 1M hydrochloric acid in ethyl acetate dropwise (24 mL, 24 mmol). The reaction mixture was stirred at 0 C. for one hour then vacuum filtered to give the desired product as a slightly off white solid (1.97 g, 9.2 mmol). 1H NMR (400 MHz, DMSO-d6) delta 10.08 (s, 1H), 9.18 (s, 3H), 8.09 (s, 1H), 8.01 (d, J=7.9 Hz, 1H), 7.91 (d, J=7.9 Hz, 1H), 7.79-7.73 (m, 1H), 5.03-4.91 (m, 4H).

The synthetic route of 3-Bromobenzaldehyde Diethyl Acetal has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AMGEN INC.; CYTOKINETICS, INC.; Ashcraft, Luke; Boezio, Alessandro; Butler, John; Chandra, Aroop; Chuang, Chihyuan; Collibee, Scott E.; Debenedetto, Mikkel; DiMassa, Vincent; Graceffa, Russell; Malinowski, Justin; Moebius, David; Morgan, Bradley P.; Payette, Joshua; Romero, Antonio; St. Jean, JR., David; Vargas, Richard; Yeoman, John; Zhang, Hanmo; (146 pag.)US2019/77793; (2019); A1;,
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Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 5111-65-9, name is 2-Bromo-6-methoxynaphthalene, This compound has unique chemical properties. The synthetic route is as follows., name: 2-Bromo-6-methoxynaphthalene

Step 21.2: 6-methoxy-naphthalen-2-ylamine A solution of 2-bromo-6-methoxy-naphthalene (237 mg, 1 mmol), Pd (dba)2 mg, 0.05 mmol), tri-t-buthylphosphonium tetrafluoroborate (14 mg, 0.05 mmol), and lithium bis (trimethylsilyl)amide (1 M in hexane, 1.1 mL, 1.1 mmol) is stirred in toluene (2.5 mL) under argon for 6 h. The reaction mixture is taken in diethyl ether (20 mL), and quenched with 1 M HCI. The organic phase is extracted with water, the combined aqueous phases are treated with 1 M sodium hydroxide and extracted with DCM. The combined organic phases are dried over magnesium sulfate, the solvent is evaporated in vacuo and the residue is purified by column flash chromatography on silica gel (ethyl acetate) to afford 6-methoxy- naphthalen-2-ylamine (110 mg, 64 %), HPLC tR : 3.07, (M+H) + = 173.9.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 5111-65-9.

Reference:
Patent; NOVARTIS AG; NOVARTIS PHARMA GMBH; WO2005/97135; (2005); A2;,
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Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 366-99-4, name is 3-Fluoro-4-methoxyaniline, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C7H8FNO

Step C: 2,5-Difluoro-lambda/-{3-[(2-{[3-fluoro-4-(methyloxy)phenyl]amino}-4- pyrimidinyl)acetyl]phenyl}benzamide; To a solution containing 2.4 g (6.2 mmol) of lambda/-{3-[(2-chloro-4- pyrimidinyl)acetyl]phenyl}-2,5-difluorobenzamide and 60 mL of i-PrOH was added 0.92 g (6.5 mmol) of 3-fluoro-4-(methyloxy)phenyl amine and 0.1 mL of cone HCI. The reaction mixture was heated at 80 0C for 20 min, then diluted with an additional 60 mL of i-PrOH and heated at 90 0C for 13 h. The reaction mixture was allowed to cool to rt, then filtered. The filter cake was collected, slurried in DCM, and neutralized by the addition of aqueous NaHCO3. The organic layer was separated and the aqueous layer was further extracted with DCM. The combined organic layers were dried over MgSO4, filtered, and concentrated under recduced pressure. The residue was subjected to silica gel chromatography to give 1.76 g (59percent) of the title compound of Step C as a yellow solid: 1H-NMR (d6-DMSO, 400 MHz) delta 10.64 (s, 1 H), 9.83 (s, 1 H), 8.31 (d, 1 H1 J = 5.3 Hz), 8.25 (s, 1 H), 7.77 (d, 1 H1 J = 8.4 Hz), 7.65-7.69 (m, 1 H), 7.61 (d, 1 H1 J = 7.7 Hz), 7.53-7.59 (m, 1 H)1 7.42-7.47 (m, 4 H), 7.27 (d, 1 H, J = 9.2 Hz)1 7.13 (dd, 1 H1 J = 9.5 Hz and 9.5 Hz), 6.64 (d, 1 H, J = 5.3 Hz), 6.20 (s, 1), and 3.80 (s, 3 H), ; ESIMS: 561.07 (M+H+).

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 366-99-4.

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2009/76140; (2009); A1;,
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Related Products of 1758-46-9, A common heterocyclic compound, 1758-46-9, name is 2-Phenoxyethylamine, molecular formula is C8H11NO, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

General procedure: To 2.45mmol of carboxylic acid derivatives (47) dissolved in 0.7mL of dry pyridine were added 0.1mL of phosphorous oxychloride. The mixture was led to?10¡ãC and then was added 39.2mmol of the appropriate amine or alcohol. The reaction was stirred at room temperature for 16h, then was added water and the product extracted with ethylacetate. The organic layer was washed with a NaHCO3 solution, dried and concentrated. The residue was purified by flash chromatography (Ethyl acetate 9: Light Petroleum 1).

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Article; Federico, Stephanie; Margiotta, Enrico; Salmaso, Veronica; Pastorin, Giorgia; Kachler, Sonja; Klotz, Karl-Norbert; Moro, Stefano; Spalluto, Giampiero; European Journal of Medicinal Chemistry; vol. 157; (2018); p. 837 – 851;,
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Related Products of 1163-19-5, In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 1163-19-5 as follows.

Using CdSe quantum dots as photocatalyst, take 10 mL of quantum dot stock solution, add appropriate amount of hydrochloric acid, centrifuge, discard the supernatant to retain solids, and redistribute the quantum dot solids to 4 mL of N,N-dimethylformamide (DMF). The concentration of the quantum dots was 2.47¡Á10-5 M; decabromodiphenyl ether (0.05 mmol) and triethylamine (2.5 mmol) were added to DMF, the rubber stopper was sealed, and the atmosphere was degassed for 20 min to remove the system. The oxygen in the room was irradiated for 24 hours at room temperature with an LED lamp (lambda > 460 nm). After the reaction, the yield and selectivity of diphenyl ether were determined by GC (FID) using diphenylacetonitrile as an internal standard. The debromination efficiency of decabromodiphenyl ether was determined by ion chromatography using sodium chloride as an internal standard. The experimental results show that decabromodiphenyl ether can be completely removed by quantum dot photocatalytic reduction and dehalogenation hydrogenation. The debromination efficiency is 65%, the yield of diphenyl ether is 54%, and the selectivity is as high as 83%.

According to the analysis of related databases, 1163-19-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Chinese Academy Of Sciences Physics And Chemistry Technology Institute; Zhang Liping; Huang Maoyong; Wu Lizhu; Li Xubing; Xin Zhikun; (9 pag.)CN110204425; (2019); A;,
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Adding a certain compound to certain chemical reactions, such as: 24988-36-1, name is 1,5-Dibromo-2,4-dimethoxybenzene, belongs to ethers-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 24988-36-1, Computed Properties of C8H8Br2O2

2,4-dibromo-1,5-dimethoxybenzene (88.8 g, 300 mmol), 2-fluorophenyl boric acid (100.7 g, 720 mmol), 2 M aqueous solution of Na2CO3 (600 mL), Pd[PPh3]4 (6.73 g, 6 mmol), DME (150 mL), and toluene (150 mL) were loaded into a three-necked flask, and the mixture was refluxed under an Ar atmosphere for 36 hours. After the completion of the reaction, the obtained solution was cooled to room temperature. The resultant sample was transferred to a separating funnel, and water (500 mL) was charged into the funnel. Then, the mixture was extracted with toluene. The extract was dried with MgSO4, and was then filtered and concentrated. The resultant sample was purified by silica gel column chromatography. The purified product was concentrated to dryness, and was then recrystallized, whereby a white solid was obtained in an amount of 86.5 g in 88% yield. FD-MS analysis C20H16F2O2: theoretical value 326, observed value 326

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; Idemitsu Kosan Co., Ltd.; EP2301926; (2011); A1;,
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Reference of 36805-97-7, In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 36805-97-7 as follows.

1 ,1-Di-tert-butoxy-W,A/-dimethylmethanamine (1.03 ml, 4.30 mmol) was added to a suspension of 2-({[(benzyloxy)carbonyl]amino}methyl)-1 -ethyl-1 H-1 ,3-benzodiazole-6- carboxylic acid, Intermediate 39 (380 mg, 1.08 mmol) in toluene (10 ml). The reaction was heated at 80 C for 2 h then allowed to cool to RT. 1 ,1-Di-tert-butoxy-A/,/v- dimethylmethanamine (1.03 ml, 4.30 mmol) was added then the reaction was heated at 80 C for 3 h then allowed to cool to RT. 1 ,1-Di-terf-butoxy-A/,W-dimethylmethanamine (1.03 ml, 4.30 mmol) was added then the reaction was heated at 110 C for 1 h then allowed to cool to RT. The reaction mixture was diluted with EtOAc (20 ml) then washed with water (2 x 20 ml), saturated aq. NaHC03 solution (2 x 20 ml) and brine (10 ml), then dried over Na2S04, filtered and evaporated to afford an orange solid (510 mg). The crude material was purified by flash column chromatography on a silica column (25 g). The column was eluted with EtOAc: heptane, increasing the gradient linearly from 0:100 to 50:50 over 10 column volumes. The desired fractions were combined and evaporated to yield the product as a white solid (320 mg, 72%).1H NMR (500 MHz, DMSO-de) delta 8.07 (s, 1 H), 7.98 (t, J = 5.8 Hz, 1 H), 7.77 (dd, J = 8.4, 1.3 Hz, 1 H), 7.64 (d, J = 8.4 Hz, 1 H), 7.41 – 7.12 (m, 5H), 5.07 (s, 2H), 4.55 (d, J = 5.9 Hz, 2H), 4.38 – 4.24 (m, 2H), 1.58 (s, 9H), 1.29 (t, J = 7.1 Hz, 3H). LC/MS (System A): m/z (ESI+) = 4 0 [MH+], R, = 1.17 min, UV purity = 99%.

According to the analysis of related databases, 36805-97-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ENTERPRISE THERAPEUTICS LIMITED; MCCARTHY, Clive; HARGRAVE, Jonathan David; HAY, Duncan Alexander; SCHOFIELD, Thomas Beauregard; WENT, Naomi; (111 pag.)WO2017/221008; (2017); A1;,
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